The Cost of Playing by the Rules: Why I Stopped Trying to Fix Systems from Within
Survival isn’t the same as freedom. And mastery of a broken system isn’t liberation.
Over the past year, I’ve been slowly, painfully divesting from the roles, institutions, and identities that rewarded me for staying small and playing by the rules. Not because I failed in those spaces—but because I finally realized I couldn’t change them from within.
This essay is about the quiet grief of letting go of systems you were good at. The strange comfort of structures that extract from you, even as they praise your efficiency. And the real risk of building something that doesn’t exist yet.
We’re not here to fix systems that weren’t built for us. We’re here to build something entirely new.
Momentum vs. Meaning: My Business Update No One Asked For
in the quiet that followed my first six months of building this business, I realized something that felt both painfully obvious and completely disorienting: Progress isn’t always proof.
Sometimes it’s just motion. And sometimes that motion is compounding harm you’ve trained yourself not to feel.
This is the update no one asked for: the one without a brag slide, without a funnel breakdown, without a viral win to report. Just the truth about what I’ve been building—and what I’m no longer willing to sacrifice in the name of momentum.
If you’ve been wondering whether it’s possible to build something meaningful without burning out, selling out, or speeding up beyond your own nervous system… this post is for you.
Can You Build a Business and Still Take Time Off? I Tried.
While launching a new partnership and leading a 70,000-word body of work, I took two weeks off—and questioned everything I thought I knew about ambition, leadership, and sustainability. This final installment of COO-fessions isn’t a recap. It’s a reflection on what it really takes to build meaningful work without burning out, to lead without performing, and to practice the future we say we believe in—before it’s fully safe to live it. If you’ve ever wondered whether it’s possible to grow without disappearing, this one’s for you.
You don’t need a perfect plan. You need a system that lets you adjust.
Slack pings at midnight, launch dates sliding, “got a sec?” turning into an hour—you’re not alone. Your ambition isn’t the issue; the Frankenstein backend holding it up is.Trade scrappy ops for systems that course-correct in real time. If you’re tired of gripping the wheel with white knuckles, I wrote this one for you.
Your Culture Isn’t Toxic—It’s Misaligned. And That’s Fixable.
Emotional intelligence isn’t the problem—it’s the system that leans on it too hard. When care becomes a substitute for structure, even the most values-driven culture starts to crack. Here’s how to spot the quiet patterns of misalignment before they turn into lower team morale, team churn, Sunday Scaries, and declining profits—and what to redesign instead.
You Can’t Build a Regenerative Business from a Dysregulated Body
Success that requires you to outrun your own nervous system isn’t success—it’s self-abandonment dressed up as productivity. In a world where ICE raids happen before dawn and global conflicts escalate by the hour, we’re still expected to clock 40-plus hours, curate “magic,” and never admit the weight. This post names the cost of high-functioning burnout, exposes how urgency culture keeps us performing credibility, and asks: What if leadership started with being regulated, present, and fully human? If you’ve mastered holding it all together but feel yourself disappearing, this one’s for you.
Leading from Conviction—Not Control
If you don’t choose how you lead, urgency will choose for you. When things move fast, it’s easy to default to control. You centralize decisions. You over-function. You try to protect your team—or push them harder—thinking it’ll keep things on track. But those shortcuts come at a cost. In this post, we unpack what it really means to lead from conviction instead of control—and why power with beats power over, every time.
Read on if you’ve been moving fast, but want to make sure you’re still moving in alignment.
Ethical branding doesn’t equal equity.
You can have the perfect values page, the inclusive language, the beautifully-branded DEI statement—and still be leading inside a system that quietly extracts, silences, and burns people out.
This is about what happens when the performance outpaces the practice. And what it really takes to build something aligned underneath the language.
What If Your Zone of Genius Is Costing Your Team Theirs?
What if your alignment is built on someone else’s exhaustion? Zone of genius isn’t about who works hardest—it’s about who’s allowed to work in a way that’s aligned. This blog breaks open the myth of genius and asks: what are you building, really?
We Weren’t Trained to Lead. We Were Trained to Serve Power.
Some of us were raised to take power. Others were raised to protect it. That uneasy feeling you get when you lead? It’s not insecurity—it’s misalignment. If you’ve been told your empathy makes you weak or your clarity makes you harsh—you’re not the problem. But the system might be. You’re not behind. You’re just unlearning.
The Cost of Leading Inside Broken Systems
You did everything “right”—and it still doesn’t feel good. Maybe it’s not you. Maybe it’s the system. This piece explores the hidden cost of leading inside models that were never built for us to thrive in. It’s a closer look at how misalignment shows up—and what it means to lead without losing yourself.
The Bypass That’s Keeping Us From Building Better
“It’s just business” is a lie we’ve told ourselves for too long. Let’s unpack how spiritual bypassing shows up as “business bypassing” in leadership and business—and why building better means facing the hard stuff, not hiding behind strategy.
You built something with a soul. Now let’s build it a spine.
Somewhere between year 3 and year 10, something starts to crack. The business works — on paper. But behind the scenes? You’re still holding it all together. This isn’t a failure of ambition. It’s a failure of alignment. Let’s talk about how to grow differently.
You’re Not Out of Capacity. You’re Out of Alignment.
Your business “works.” On paper. But it’s starting to feel brittle. This isn’t a bandwidth issue — it’s a misalignment issue. Here’s what to do when the business you built stops feeling like the one you meant to build.
Beyond the PIP: What to Do When Someone Isn’t Growing with You
When someone on your team isn’t growing with you, the easy temptation is to blame them—or worse, to avoid the conversation altogether.
But leadership isn’t just about compassion. It’s about clarity.
If we’re serious about interrupting cycles of extraction and burnout, we need more than good intentions. We need real tools. Because misalignment doesn’t usually show up as a dramatic blowout. It creeps in slowly: missed deadlines, misunderstood priorities, mounting tension.
Shots Fired: When Feedback Isn't Feedback at All
Not all feedback is created equal. Sometimes it's not about growth—it's about control. If you’ve ever been blindsided by a “surprise” write-up, you’re not alone. Let’s talk about why most performance management breaks trust—and what to build instead.
The Invisible Gap That Sinks Great Teams
Big visions don’t move mountains—bulldozers do. If you’re feeling stuck between what you see and what your team can carry, it’s not a leadership flaw. It’s a systems gap. Here’s how to bridge it—with clarity, not chaos.
How Do We Build Something Better?
Most of us are still working inside the very system we want to change. So how do we start building something better—without burning it all down? In Part 5, I’m exploring the shift from burnout to regeneration. Because naming the problem isn’t enough. Let’s rebuild.
When the System Expects Your Overwork
You’re told to have balance. But the system still rewards burnout. What do you do when your workplace says all the right things—but still quietly expects you to break yourself to keep things running? Here’s how to protect your capacity when the system won’t.
“This Isn’t Working”
A newsletter for people who know we can do better.
So much of how we’ve been taught to lead, work, and succeed isn’t actually working—for us, for our teams, or for the world we want to build.
Each week, This Isn’t Working digs into the misalignment we feel in work, leadership, and ambition—and, more importantly, what we can do about it.
What you can expect:
Candid insights on leadership, power, and navigating change
Strategies for building differently—without burnout or or auto-exploitation
A behind-the-scenes look at what’s working (and what’s not)
Drop your email, and let’s build something better.